Vacation rentals in Northwest Side

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Top-rated vacation rentals in Northwest Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Apartment in Irving Park

4.92 out of 5 average rating, 584 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.

Apr 17 – 24

R2,488 ZAR per night
Guest favorite

Guest suite in Portage Park

4.93 out of 5 average rating, 346 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Mar 5 – 12

R2,115 ZAR per night
Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 116 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

May 23 – 30

R2,054 ZAR per night

Popular amenities for Northwest Side vacation rentals

Other great vacation rentals in Northwest Side

Guest favorite

Apartment in Jefferson Park

4.92 out of 5 average rating, 132 reviews

Amazing 2 bedroom apartment on prime location

Sep 1 – 8

R1,943 ZAR per night
Guest favorite

Apartment in Irving Park

4.97 out of 5 average rating, 249 reviews

Spacious 1BR apartment in a central location

Jul 8 – 15

R1,821 ZAR per night
Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 335 reviews

Sunny Logan Square Artists' home

Jan 5 – 12

R2,073 ZAR per night
Guest favorite

Apartment in Logan Square

4.87 out of 5 average rating, 481 reviews

Logan Square Studio

Feb 24 – Mar 3

R1,940 ZAR per night
Guest favorite

Guest suite in Logan Square

4.97 out of 5 average rating, 232 reviews

Stylish Studio in Historic Logan Square

Aug 23 – 30

R2,896 ZAR per night
Guest favorite

Apartment in Portage Park

4.95 out of 5 average rating, 100 reviews

Comfortable, modern apartment 20 Min from Downtown

Dec 19 – 26

R2,189 ZAR per night
Guest favorite

Guest suite in Chicago

4.92 out of 5 average rating, 52 reviews

The Abode Chicago - Portage Park- 20min> O'Hare

R1,758 ZAR per night
Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 26 reviews

King Size Sleep Number Bed in Cozy Home w/ No fees

Nov 20 – 27

R2,031 ZAR per night
Superhost

Apartment in Portage Park

4.85 out of 5 average rating, 72 reviews

Classic Chicago Bungalow Garden Unit

Nov 8 – 15

R1,627 ZAR per night
Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 45 reviews

Comfy & Private Chicago Studio

Aug 8 – 15

R2,026 ZAR per night
Guest favorite

Guest suite in Portage Park

4.93 out of 5 average rating, 75 reviews

Eddy Street Upstairs Apartment

May 1 – 8

R1,624 ZAR per night
Guest favorite

Apartment in Portage Park

4.94 out of 5 average rating, 18 reviews

Top Floor Portage Park Lookout

Aug 18 – 25

R2,600 ZAR per night

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